Indole and benzimidazole derivatives

A compound of formula IC:

• wherein
• W is ═CH— or ═N—;
• p is equal to 1, 2 or 3;
• R9 is alkyl or substituted alkyl;
• R11 and R12, together with the nitrogen atom bound thereto join to form a group selected from the group consisting of heterocyclic, substituted heterocyclic, heteroaryl, and substituted heteroaryl;
• R13 is -L1-A3, wherein L1 is —S(O)r— where r is 1 or 2 or C1 to C2 straight chain alkylene, and A3 is selected from the group consisting of aryl, substituted aryl, heteroaryl, and substituted heteroaryl;
• each R14 is independently selected from the group consisting of halo, C2 to C3 alkynyl, C2 to C3 alkenyl, C1 to C5 alkyl, C1 to C3 alkoxy, and phenyl;
• or pharmaceutically acceptable salts, esters or prodrugs thereof;
• with the proviso that when W is ═N—, and A3 is substituted phenyl, said substituted phenyl does not include an ortho substituent of the formula -Q-NR7R8 where Q is a bond, C1 to C3 alkyl, C2 to C3 alkenyl, C2 to C3 alkynyl and R7 and R8 are independently C1 to C8 alkyl or C1 to C8 cycloalkyl optionally substituted with 1 to 3 substituents selected from the group consisting of hydroxy, halo, amino, cyano, nitro, C1 to C8 alkyl, C1 to C8 cycloalkyl, halo C1 to C8 alkyl, C1 to C8 alkoxy, halo C1 to C8 alkoxy, or R7 and R8 jointly with the nitrogen atom to which they are bound form an optionally substituted 3- to 7-membered heterocyclic or an optionally substituted 3- to 7-membered heteroaryl.

A compound of formula IA′:

• wherein:
• R1 is selected from the group consisting of aminoacyl, acylamino, carboxyl, carboxyl ester, aryl, and alkyl optionally substituted with hydroxy or halo;
• R2 is selected from the group consisting of hydrogen, optionally substituted alkyl, and aryl;
• R3 and R4, together with the nitrogen atom bound thereto, form a group selected from the group consisting of heterocyclic, substituted heterocyclic, heteroaryl, and substituted heteroaryl;
• R5 is selected from the group consisting of 2,4-difluorobenzyl;
• 2-methylbenzyl;
• 3-(methylamido)benzyl;
• 3,5-difluorobenzyl;
• 3-chlorobenzyl;
• 3-fluorobenzyl;
• 3-hydroxybenzyl;
• 3-methylbenzyl;
• 4-chlorobenzyl;
• 4-methylbenzyl;
• benzyl;
• and thiazol-4-ylmethyl;
• each R6 is independently selected from the group consisting of acyl, acylamino, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, alkoxy, substituted alkoxy, amino, substituted amino, aminoacyl, aryl, substituted aryl, aryloxy, substituted aryloxy, carboxyl, carboxyl ester, cyano, cycloalkyl, substituted cycloalkyl, halo, heteroaryl, substituted heteroaryl, heteroaryloxy, substituted heteroaryloxy, heterocyclic, substituted heterocyclic, heterocyclyloxy, substituted heterocyclyloxy, hydroxy, nitro, thiol, alkylthio, substituted alkylthio, arylthio, substituted arylthio, heteroarylthio, and substituted heteroarylthio;
• p is equal to 0, 1, 2 or 3;
• or pharmaceutically acceptable salts, esters and prodrugs thereof.

A compound of formula IA′:

• wherein:
• R1 is selected from the group consisting of ethyl, isopropyl, t-butyl, and phenyl;
• R2 is selected from the group consisting of hydrogen, optionally substituted alkyl, and aryl;
• R3 and R4, together with the nitrogen atom bound thereto, form a group selected from the group consisting of heterocyclic, substituted heterocyclic, heteroaryl, and substituted heteroaryl;
• R5 is -L-A1 where L is selected from the group consisting of —S(O)r— where r is one or two and C1 to C2 straight chain alkylene, optionally substituted with hydroxy, halo and acylamino;
• A1 is phenyl or substituted phenyl;
• each R6 is independently selected from the group consisting of acyl, acylamino, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, alkoxy, substituted alkoxy, amino, substituted amino, aminoacyl, aryl, substituted aryl, aryloxy, substituted aryloxy, carboxyl, carboxyl ester, cyano, cycloalkyl, substituted cycloalkyl, halo, heteroaryl, substituted heteroaryl, heteroaryloxy, substituted heteroaryloxy, heterocyclic, substituted heterocyclic, heterocylyloxy, substituted heterocyclyloxy, hydroxy, nitro, thiol, alkylthio, substituted alkylthio, arylthio, substituted arylthio, heteroarylthio, and substituted heteroarylthio;
• p is equal to 0, 1, 2 or 3;
• or pharmaceutically acceptable salts, esters and prodrugs thereof;
• with the proviso that when A1 is substituted phenyl, said substituted phenyl does not include an ortho substituent of the formula -Q-NR7R8 where Q is a bond, C1 to C3 alkyl, C2 to C3 alkenyl, C2 to C3 alkynyl and R7 and R8 are independently C1 to C8 alkyl or C1 to C8 cycloalkyl optionally substituted with 1 to 3 substituents selected from the group consisting of hydroxy, halo, amino, cyano, nitro, C1 to C8 alkyl, C1 to C8 cycloalkyl, halo C1 to C8 alkyl, C1 to C8 alkoxy, halo C1 to C8 alkoxy, or R7 and R8 jointly with the nitrogen atom to which they are bound form an optionally substituted 3- to 7-membered heterocyclic or an optionally substituted 3- to 7-membered heteroaryl.

A compound of formula IA′:

• wherein:
• R1 is selected from the group consisting of aminoacyl, acylamino, carboxyl, carboxyl ester, aryl, and alkyl optionally substituted with hydroxy or halo;
• R2 is selected from the group consisting of hydrogen, optionally substituted alkyl, and aryl;
• R3 and R4, together with the nitrogen atom bound thereto, form a group selected from the group consisting of heterocyclic, substituted heterocyclic, heteroaryl, and substituted heteroaryl;
• R5 is -L-A1 where L is selected from the group consisting of —S(O)r— where r is one or two and C1 to C2 straight chain alkylene, optionally substituted with hydroxy, halo and acylamino;
• A1 is phenyl or substituted phenyl;
• each R6 is independently selected from the group consisting of acyl, acylamino, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, alkoxy, substituted alkoxy, amino, substituted amino, aminoacyl, aryl, substituted aryl, aryloxy, substituted aryloxy, carboxyl, carboxyl ester, cyano, cycloalkyl, substituted cycloalkyl, halo, heteroaryl, substituted heteroaryl, heteroaryloxy, substituted heteroaryloxy, heterocyclic, substituted heterocyclic, heterocyclyloxy, substituted heterocyclyloxy, hydroxy, nitro, thiol, alkylthio, substituted alkylthio, arylthio, substituted arylthio, heteroarylthio, and substituted heteroarylthio;
• p is 1;
• or pharmaceutically acceptable salts, esters and prodrugs thereof;
• with the proviso that when A1 is substituted phenyl, said substituted phenyl does not include an ortho substituent of the formula -Q-NR7R8 where Q is a bond, C1 to C3 alkyl, C2 to C3 alkenyl, C2 to C3 alkynyl and R7 and R8 are independently C1 to C8 alkyl or C1 to C8 cycloalkyl optionally substituted with 1 to 3 substituents selected from the group consisting of hydroxy, halo, amino, cyano, nitro, C1 to C8 alkyl, C1 to C8 cycloalkyl, halo C1 to C8 alkyl, C1 to C8 alkoxy, halo C1 to C8 alkoxy, or R7 and R8 jointly with the nitrogen atom to which they are bound form an optionally substituted 3- to 7-membered heterocyclic or an optionally substituted 3- to 7-membered heteroaryl.

A compound of formula IC′:

• wherein
• p is equal to 0, 1, 2 or 3;
• R9 is alkyl or substituted alkyl;
• R11 and R12, together with the nitrogen atom bound thereto, join to form a group selected from the group consisting of heterocyclic, substituted heterocyclic, heteroaryl, and substituted heteroaryl;
• R13 is -L1-A3, wherein L1 is —S(O)r— where r is 1 or 2 or C1 to C2 straight chain alkylene, and A3 is phenyl or substituted phenyl;
• each R14 is independently selected from the group consisting of halo, C2 to C3 alkynyl, C2 to C3 alkenyl, C1 to C5 alkyl, C1 to C3 alkoxy, and phenyl;
• or pharmaceutically acceptable salts, esters or prodrugs thereof;
• with the proviso that when A3 is substituted phenyl, said substituted phenyl does not include an ortho substituent of the formula -Q-NR7R8 where Q is a bond, C1 to C3 alkyl, C2 to C3 alkenyl, C2 to C3 alkynyl and R7 and R8 are independently C1 to C8 alkyl or C1 to C8 cycloalkyl optionally substituted with 1 to 3 substituents selected from the group consisting of hydroxy, halo, amino, cyano, nitro, C1 to C8 alkyl, C1 to C8 cycloalkyl, halo C1 to C8 alkyl, C1 to C8 alkoxy, halo C1 to C8 alkoxy, or R7 and R8 jointly with the nitrogen atom to which they are bound form an optionally substituted 3- to 7-membered heterocyclic or an optionally substituted 3- to 7-membered heteroaryl.